Reaction of  N -sulfonyl-1,4-benzoquinone imines with sodium azide

S. A. Konovalova; A. P. Avdeenko; S. V. Shelyazhenko; V. V. Pirozhenko; O. N. Mikhailichenko; A. L. Yusina

doi:10.1134/S1070428016010048

Reaction of N-sulfonyl-1,4-benzoquinone imines with sodium azide

Authors: Konovalova S.A.¹, Avdeenko A.P.¹, Shelyazhenko S.V.², Pirozhenko V.V.², Mikhailichenko O.N.¹, Yusina A.L.¹
Affiliations:
1. Donbass State Engineering Academy
2. Institute of Organic Chemistry
Issue: Vol 52, No 1 (2016)
Pages: 15-24
Section: Article
URL: https://journal-vniispk.ru/1070-4280/article/view/213453
DOI: https://doi.org/10.1134/S1070428016010048
ID: 213453

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Abstract

Depending on the conditions and the order of addition of the reactants, reactions of N-sulfonyl-1,4-benzoquinone imines with sodium azide afforded N-(3-azido-4-hydroxyphenyl)alkane(arene)sulfonamides, N-(3-azido-4-oxocyclohexa-2,5-dienylidene)alkane(arene)sulfonamides, and N-(3,5-diazido-4-hydroxyphenyl)-alkanesulfonamides. Quantum chemical calculations showed that the reactions begin with addition of azide ion to the quinone imine.